4-Pentynoic acid, 1,1-dimethylethyl ester → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(4-t-butoxycarbonyl-1-butynyl)-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369069Notes

Reaction equation

HRID 1369069 reaction equation
[CH2:1]([N:3]([CH2:32][CH3:33])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12](I)[CH:13]=2)[C:8]([OH:30])([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:7]1=[O:31])[CH3:2].[C:34]([O:38][C:39]([CH2:41][CH2:42][C:43]#[CH:44])=[O:40])([CH3:37])([CH3:36])[CH3:35]>>[CH2:1]([N:3]([CH2:32][CH3:33])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12]([C:44]#[C:43][CH2:42][CH2:41][C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])[CH:13]=2)[C:8]([OH:30])([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:7]1=[O:31])[CH3:2]

Participants

3

Reactant 2

HCID 108773414-Pentynoic acid, 1,1-dimethylethyl esterHCID 118278961-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole

Product 1

HCID 185185541-(2-Diethylaminoethyl)-4-trifluoromethyl-6-(4-t-butoxycarbonyl-1-butynyl)-3-hydroxy-3-(2-naphthyl)oxindoleYield 82%

Procedure

The title compound (34.9 mg, 82%) was prepared from 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole of Example 48 (40.9 mg, 0.0720 mmol) and 4-t-butoxycarbonyl-1-butyne by the procedure similar to that described in Reference Example 21.

Sources & evidence

ORD record
ord-9e9fbdedf6fc41c88f484378cb7d8890
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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